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Chemical Compound Review

Sulfobetaine     2-dimethylsulfonioethanoate

Synonyms: CCRIS 5467, AG-K-62316, CHEBI:16471, KST-1A5758, KST-1A5759, ...
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Disease relevance of carboxymethyl-dimethyl-sulfonium


High impact information on carboxymethyl-dimethyl-sulfonium

  • Q-band electron nuclear double resonance (ENDOR) and X-band EPR of the sulfobetaine 12 heat-treated cytochrome c oxidase complex [4].
  • The observation of sulfobetaine specifically bound to the protein active site was unexpected and is unique to this structure as far as we are aware [5].
  • We prepared a washed cell membrane fraction that was insoluble in 134 mM nondetergent sulfobetaine and then extracted proteins using mixtures of detergents in a stepwise manner [6].
  • The sulfobetaine 12 modified enzyme is no longer capable of undergoing the recently reported conformational transition in which the tryptophan fluorescence changes upon reduction of the low-potential metal centers [7].
  • Despite the relatively low chaotropic nature of cations compared with anions, the retention data shows that cations are retained in this system predominantly due to a chaotropic interaction with the inner charge, analogous to anions in a system where the C18 column is coated with a sulfobetaine-type surfactant [8].

Biological context of carboxymethyl-dimethyl-sulfonium

  • Furthermore, the zwitterionic and biomimetic nature of sulfobetaine and the ease of SBMA preparation make SBMA-based materials very attractive for a wide range of applications [9].
  • They complement the more classical sulfobetaine detergents to widen the scope of useful detergents for the solubilization of membrane proteins in proteomics [10].

Anatomical context of carboxymethyl-dimethyl-sulfonium


Associations of carboxymethyl-dimethyl-sulfonium with other chemical compounds


Gene context of carboxymethyl-dimethyl-sulfonium

  • This type 2 copper EPR spectrum is identical to the EPR spectrum of CuB reported for the isolated cytochrome bo3 complex from Escherichia coli; and to the EPR spectrum reported for the sulfobetaine 12 heat-treated cytochrome c oxidase complex [14].

Analytical, diagnostic and therapeutic context of carboxymethyl-dimethyl-sulfonium


  1. Molecular weight determination of an active photosystem I preparation from a thermophilic cyanobacterium, Synechococcus elongatus. Schafheutle, M.E., Setliková, E., Timmins, P.A., Johner, H., Gutgesell, P., Setlik, I., Welte, W. Biochemistry (1990) [Pubmed]
  2. Nanomolar levels of dimethylsulfoniopropionate, dimethylsulfonioacetate, and glycine betaine are sufficient to confer osmoprotection to Escherichia coli. Cosquer, A., Pichereau, V., Pocard, J.A., Minet, J., Cormier, M., Bernard, T. Appl. Environ. Microbiol. (1999) [Pubmed]
  3. Succinate-mediated catabolite repression control on the production of glycine betaine catabolic enzymes in Pseudomonas aeruginosa PAO1 under low and elevated salinities. Diab, F., Bernard, T., Bazire, A., Haras, D., Blanco, C., Jebbar, M. Microbiology (Reading, Engl.) (2006) [Pubmed]
  4. Q-band electron nuclear double resonance (ENDOR) and X-band EPR of the sulfobetaine 12 heat-treated cytochrome c oxidase complex. Musser, S.M., Fann, Y.C., Gurbiel, R.J., Hoffman, B.M., Chan, S.I. J. Biol. Chem. (1997) [Pubmed]
  5. Structures for the potential drug target purine nucleoside phosphorylase from Schistosoma mansoni causal agent of schistosomiasis. Pereira, H.D., Franco, G.R., Cleasby, A., Garratt, R.C. J. Mol. Biol. (2005) [Pubmed]
  6. Profiling and comprehensive expression analysis of ABC transporter solute-binding proteins of Bacillus subtilis membrane based on a proteomic approach. Bunai, K., Ariga, M., Inoue, T., Nozaki, M., Ogane, S., Kakeshita, H., Nemoto, T., Nakanishi, H., Yamane, K. Electrophoresis (2004) [Pubmed]
  7. Conversion of CuA to a type II copper in cytochrome c oxidase. Nilsson, T., Copeland, R.A., Smith, P.A., Chan, S.I. Biochemistry (1988) [Pubmed]
  8. Mechanistic studies on the separation of cations in zwitterionic ion chromatography. Cook, H.A., Dicinoski, G.W., Haddad, P.R. Journal of chromatography. A. (2003) [Pubmed]
  9. Development of biocompatible interpenetrating polymer networks containing a sulfobetaine-based polymer and a segmented polyurethane for protein resistance. Chang, Y., Chen, S., Yu, Q., Zhang, Z., Bernards, M., Jiang, S. Biomacromolecules (2007) [Pubmed]
  10. Evaluation of nonionic and zwitterionic detergents as membrane protein solubilizers in two-dimensional electrophoresis. Luche, S., Santoni, V., Rabilloud, T. Proteomics (2003) [Pubmed]
  11. An improved procedure for purifying 5'-nucleotidase from various sources. Evidence for tissue and species differences in their molecular mass and affinity for F-actin. Dieckhoff, J., Knebel, H., Heidemann, M., Mannherz, H.G. Eur. J. Biochem. (1985) [Pubmed]
  12. Matrilysin: expression, purification, and characterization. Soler, D., Nomizu, T., Brown, W.E., Shibata, Y., Auld, D.S. J. Protein Chem. (1995) [Pubmed]
  13. Potential of the sulfobetaine detergent Zwittergent 3-12 as a desorbing agent in biospecific and bioselective affinity chromatography. Nollstadt, K.H., Karkhanis, Y.D., Gnozzio, M.J., Crane, M.S., Gurnett, A.M., Schmatz, D.M., Turner, M.J. J. Chromatogr. (1989) [Pubmed]
  14. The EPR spectrum for CuB in cytochrome c oxidase. Pezeshk, A., Torres, J., Wilson, M.T., Symons, M.C. J. Inorg. Biochem. (2001) [Pubmed]
  15. Immunization with the recombinant PorB outer membrane protein induces a bactericidal immune response against Neisseria meningitidis. Wright, J.C., Williams, J.N., Christodoulides, M., Heckels, J.E. Infect. Immun. (2002) [Pubmed]
  16. Determination of inorganic anions in human saliva by zwitterionic micellar capillary electrophoresis. Mori, M., Hu, W., Fritz, J.S., Tsue, H., Kaneta, T., Tanaka, S. Fresenius' journal of analytical chemistry. (2001) [Pubmed]
  17. Investigations into sulfobetaine-stabilized cu nanoparticle formation: toward development of a microfluidic synthesis. Song, Y., Doomes, E.E., Prindle, J., Tittsworth, R., Hormes, J., Kumar, C.S. The journal of physical chemistry. B, Condensed matter, materials, surfaces, interfaces & biophysical. (2005) [Pubmed]
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